Fifteenth-century diplomatic protocol required the city of Florence to send diplomats to congratulate both new and militarily victorious rulers. Diplomats on such missions poured praise on their triumphant allies and new rulers at friendly locations. However, political realities also meant that these diplomats would sometimes have to praise rulers whose accession or victory opposed Florentine interests. Moreover, different allies and enemies required different levels of praise. Jealous rulers compared the gifts, status, and oratory that they received from Florence to the Florentine entourages sent to their neighbors. Sending diplomats with too little or too much social status and eloquence could spell diplomatic disaster. Diplomats met these challenges by varying the style, structure, and content of their speeches. Far from formulaic pronouncements of goodwill, diplomatic orations varied from one speech to the next in order to meet the demands of the complex diplomatic world into which they fit. Contextualizing these orations reveals the subtle reservations of diplomats praising a hostile ruler, the insertion of specific citations to flatter specific audiences, and the changing intellectual and stylistic interests of humanists throughout the fifteenth century. This essay will examine the different shades of flattery practiced by Florentine diplomats and the contexts that explain these variations.